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Note | Regular issue | Vol 65, No. 5, 2005, pp.1215-1220
Published online, 1st March, 2005
DOI: 10.3987/COM-05-10344
Total Synthesis and Antioxidative Activity of Magnolamide from Magnolia coco

Wen-Fei Chiou, Chien-Chang Shen, Hsi-Jung Yu, Chang-Han Chiang, Ching-Chuan Chen, Wenyi Chang, and Ming-Jaw Don*

*National Research Institute of Chinese Medicine, 155-1, Sec. 2, Li-Nung Street, Taipei 112, Taiwan, R.O.C.


A simple total synthesis of naturally occurring magnolamide, N-[4-(2-formyl-5-hydroxymethylpyrrol-1-yl)butyl]-3-(4-hydroxy-3-methoxy- phenyl)-2-propenamide, from pyrrole-2,5-dicarbaldehyde was performed in six steps and its antioxidant activity was compared with probucol and resveratrol. Results showed that magnolamide markedly inhibited CuSO4-induced oxidation of human low-density lipoprotein (IC50 = 9.7 μM) with similar activity to probucol and resveratrol.